Triphenylphosphine → Benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl ester

HRID 1903602

Reaktionsgleichung

Reaktionsgleichung von HRID 1903602
[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[NH:18][C:17]1=[O:22])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7].[CH3:24][O:25][C:26]1[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[CH:30][C:27]=1[CH2:28]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:1][O:2][C:3](=[O:23])[CH:4]([CH:16]1[CH2:20][C:19](=[O:21])[N:18]([CH2:28][C:27]2[CH:30]=[CH:31][C:32]([O:34][CH3:35])=[CH:33][C:26]=2[O:25][CH3:24])[C:17]1=[O:22])[NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[O:7]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 817502,4-Dimethoxybenzyl alcoholHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 13105389Benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester

Produkt 1

HCID 20449787Benzyloxycarbonyl-2-[1-(2,4-dimethoxybenzyl)-2,5-dioxopyrrolidin-3-yl] glycine methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In 100 ml of tetrahydrofuran were dissolved 3.2 g of benzyloxycarbonyl-2-(2,5-dioxopyrrolidin-3-yl)glycine methyl ester, 1.8 g of 2,4-dimethoxybenzyl alcohol and 3.9 g of triphenylphosphine and under ice-cooling 2 ml of diethyl azodicarboxylate was added. The mixture was stirred at room temperature for one hour and concentrated under reduced pressure. The residue was dissolved in ethyl acetate, and the solution was washed with 5% sodium hydrogen carbonate and 10% phosphoric acid in that order and dried over sodium sulfate. The solution was concentrated under reduced pressure and the concentrate was chromatographed on a silica gel column, elution being carried out with toluene-ethyl acetate (7:3). The eluate was concentrated under reduced pressure and to the residue was added petroleum ether. The precipitate was collected by filtration and dried. Yield 1.2 g

Aufarbeitung

  1. additionwas added
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washthe solution was washed with 5% sodium hydrogen carbonate and 10% phosphoric acid in that order
  5. dry with materialdried over sodium sulfate
  6. concentrationThe solution was concentrated under reduced pressure
  7. customthe concentrate was chromatographed on a silica gel column, elution
  8. concentrationThe eluate was concentrated under reduced pressure and to the residue
  9. additionwas added petroleum ether
  10. filtrationThe precipitate was collected by filtration
  11. customdried

Quellen und Nachweise

ORD-Eintrag
ord-7a45b318a5c649daa32cb85a0cceafb2
Quelldatensatz
uspto-grants-1984_03
Patentnummer
US04436918

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